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Sodium Hydroxide → (5S,6R,7E,9E,11Z, 13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxa-7,9,11,13-hexadecatetraenoic acid

HRID 1354501
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HRID 1354501 반응식
[F:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][CH2:7][C@@H:8]([OH:28])/[CH:9]=[CH:10]/[CH:11]=[CH:12]\[CH:13]=[CH:14]\[CH:15]=[CH:16]\[C@@H:17]([OH:27])[C@@H:18]([OH:26])[CH2:19][O:20][CH2:21][C:22]([O:24]C)=[O:23])=[CH:4][CH:3]=1.[OH-].[Na+].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C@@H:8]([OH:28])/[CH:9]=[CH:10]/[CH:11]=[CH:12]\[CH:13]=[CH:14]\[CH:15]=[CH:16]\[C@@H:17]([OH:27])[C@@H:18]([OH:26])[CH2:19][O:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:29][CH:30]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 62657Potassium Phosphate, TribasicHCID 10112981Acetic acid, (((2S,3R,4E,6E,8Z,10E,12S)-13-(4-fluorophenoxy)-2,3,12-trihydroxy-4,6,8,10-tridecatetraenyl)oxy)-, methyl ester

생성물 1

HCID 10112100(5S,6R,7E,9E,11Z, 13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxa-7,9,11,13-hexadecatetraenoic acid수율 41,499.602%

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

A solution of (5S,6R,7E,9E,11Z,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxa-7,9,11,13-hexadecatetraenoic acid, methyl ester, (25 mg, 59 nMol) in methanol (6 mL) was treated with 1 N NaOH (aq) (25 μL, 25 μmol) solution and shaken and allowed to stand. Upon completion, the reaction was treated with saturated potassium monophosphate. Purification by chromatography on an HP20 column eluted with an aqueous methanol gradient gave 10 mg of (5S,6R,7E,9E,11Z,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxa-7,9,11,13-hexadecatetraenoic acid; 1H NMR (CD3OD) δ 3.6 (m, 3H), 3.88 (m, 4H), 4.18 (m, 1H), 4.52 (m, 1H), 5.84 (m, 2H), 6.03 (m, 2H), 6.34 (m, 2H), 6.74 (m, 1H), 6.95 (m, 5H) ppm.

후처리

  1. customPurification by chromatography on an HP20 column
  2. washeluted with an aqueous methanol gradient

출처 및 근거

ORD 기록
ord-70224b7cf8db429b98d5464a90bc277c
출처 데이터셋
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07223798B2

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